3-(2,4-dichlorophenyl)-6-((4-methoxyphenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole | 862245-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2,4-dichlorophenyl)-6-((4-methoxyphenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
• 英文别名: 3-(2,4-Dichlorophenyl)-6-[(4-methoxyphenoxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole；3-(2,4-dichlorophenyl)-6-[(4-methoxyphenoxy)methyl]-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
• CAS: 862245-69-0
• 化学式: C₁₇H₁₂Cl₂N₄O₂S
• 分子量: 407.28
• InChiKey: HSPVFWWSSPZDNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  161.8 °C(Solv: ethanol (64-17-5))
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲氧基苯氧乙酸 、 4-氨基-5-(2,4-二氯苯基)-4H-[1,2,4]噻唑-3-硫醇 在 三氯氧磷 作用下， 反应 6.0h， 以73%的产率得到3-(2,4-dichlorophenyl)-6-((4-methoxyphenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Novel Lead Structures for p38 MAP Kinase via FieldScreen Virtual Screening

  摘要：

  p38 MAP kinase has received considerable interest in the pharmaceutical industry and remains a valid and interesting target for the treatment of inflammation. To discover novel p38 inhibitors, we applied the ligand-based virtual screening technique, FieldScreen, to 1.2 million commercially available compounds. Fifty-eight diverse compounds were selected for biological analysis, using molecular field similarity to known inhibitors, while explicitly removing any structure that shared a scaffold with previously reported p38 inhibitors. Of these, 11 (19%) showed >= 20% inhibition of p38 at 10 mu M. We chose to prepare analogues of two distinct chemical series resulting in a potential lead compound with pIC(50) of 6.4. Modeling of SAR using FieldAlign, a ligand alignment protocol, was used to rationalize the SAR of the series of thiadiazole based inhibitors.

  DOI：

  10.1021/jm801399r

文献信息

• Novel Lead Structures for p38 MAP Kinase via FieldScreen Virtual Screening
  作者：Timothy J. Cheeseright、Melanie Holm、Frank Lehmann、Sabine Luik、Marcia Göttert、James L. Melville、Stefan Laufer

  DOI：10.1021/jm801399r

  日期：2009.7.23

  p38 MAP kinase has received considerable interest in the pharmaceutical industry and remains a valid and interesting target for the treatment of inflammation. To discover novel p38 inhibitors, we applied the ligand-based virtual screening technique, FieldScreen, to 1.2 million commercially available compounds. Fifty-eight diverse compounds were selected for biological analysis, using molecular field similarity to known inhibitors, while explicitly removing any structure that shared a scaffold with previously reported p38 inhibitors. Of these, 11 (19%) showed >= 20% inhibition of p38 at 10 mu M. We chose to prepare analogues of two distinct chemical series resulting in a potential lead compound with pIC(50) of 6.4. Modeling of SAR using FieldAlign, a ligand alignment protocol, was used to rationalize the SAR of the series of thiadiazole based inhibitors.